Herbicide

ABSTRACT

Herbicide comprising a mixture of a nitrophenol derivative and a benzothiadiazinone dioxide derivative.

United States Patent [19] Fischer et al.

[111 '3,871,864 [451 Mar. 18, 1975 HERBICIDE Inventors: Adolf Fischer, Mutterstadt; Siegfried Behrendt, Wachenheim; Bernd-l-leinrich Menck, Schilfferstadt, all of Germany Assignee: Badische Anilin & Soda-Fabrik Aktiengesellschaft, Ludwigshafen/Rhine, Germany Filed: Jan. 31, 1973 App]. No.: 328,470

Foreign Application Priority Data Feb. I4, 1972 Germany 2206861 US. Cl. 71/91, 71/122 Int. Cl A0ln 9/14 [58] Field of Search 7l/9l, 122

[56] References Cited UNITED STATES PATENTS 2,841,483 7/1958 Swezey et al. 71/122 3,130,037 4/1964 Scherer et al 7l/l22 3,708,277 l/l973 Zeidler et al. 7l/9l [57] ABSTRACT Herbicide comprising a mixture of a nitrophenol derivative and a benzothiadiazinone dioxide derivative.

2 Claims, No Drawings where R denotes hydrogen, acetyl', or chloroacetyl, R denotes lower alkyl of a maximum of 6 carbon atoms, alkoxyalkyl or chlorine, R denotes hydrogen or lower alkyl of a maximum of 4 carbon atoms, R denotes nitro or chlorine, and R denotes hydrogen, chlorine or methyl, and a compound of the formula on /SO where R denotes lower alkyl of a maximum of 4 carbon atoms, or its salts, has a better herbicidal action than its individual components.

Suitable salts are the alkali metal, alkaline earth metal, ammonium, hydroxyalkylammonium, alkylammonium, hydrazine, fatty alkylammonium, pyridine and aniline salts, and cycloalkylamine salts such as salts of sodium, lithium, potassium, calcium, iron, methylamine, trimethylamine, ethylamine, diethanolamine, ethanolamine, dimethylamine, dimethylethanolamine, hydrazine, phenylhydrazine, pyridine, ethanolamine and cyclohexylamine.

Mixtures in which the weight ratio of a b is from 1:10 to 5:1 are preferred. The rate of application is from 0.1 to 3 kg per hectare for active ingredient (a), and from 0.5 to ID kg per hectare for active ingredient (b). The mixtures are applied after the plants have developed leaves.

The herbicides may be used as solutions, emulsions, suspensions or dusts, or in the form of granules. The form of application depends entirely on the purpose for which the agents are being used; in any case it should ensure a fine distribution of the active ingredient.

For the preparation of solutions to be sprayed direct, mineral oil fractions of medium to high boiling point, such as kerosene and disel oil, further coal tar oils and oils of vegetable or animal origin, and cyclic hydrocarbons, e.g., tetrahydronaphthalene or alkylated naphthalenes are suitable.

Aqueous formulations may be prepared from emulsion concentrates, pastes or wettable powders by adding water. To prepare emulsions the ingredients as such or dissolved in a solvent may be homogenized in water or organic solvents by means of wetting or dispersing agents. Concentrates which are suitable for dilution with water may be prepared from active ingredient,

waterplantain scarlet pimpernel redroot pigweed Alisma plamago-aqualica Anagallis arvensis Amaramhus relrnflexur Amhemis spp. chamomile species Ammania spp. ammania species Arriplex spp. saltbush species Buromus umbellatus swanflower Capsella bursa pasloris shepherds purse Cemaurea cyanus cornflower Chenopodium album Chrysanthemum segemm C yperus spp.

common lambsquarters corn marigold flatsedge species F umaria offlz'inalis fumitory Galeopsis lelrahir hempnettle Galium aparine catchweed bedstraw Papaver rlweas corn poppy Polyganum spp. smartweed species Raphanus rapham'slrum wild radish Ranunculus arvensis Scirpus spp.

Senecio vulgaris Sesbania exaltata corn buttercup bulrush species common groundsel hemp sesbania Sida spinosa prickly sida Sinapis arvensis wild mustard Spergula arvensis corn spurry Stellaria media ehickweed Urtica urens Veronica spp. Vicia spp. Xanrhium spp.

burning nettle speedwell species vetch species cocklebur species without causing damage to the crop plants:

beans potatoes peas legumes peanuts alfalfa cereals clover barley lndian corn oats rice rye onions wheat EXAMPLE I In the greenhouse the plants Hordeum vulgare, Triticum aestivum, Galium aparine, Lamium amplexicaule, Vicia spp. and Stellaria media were treated at a growth height of 3 to l8 cm with the following amounts of the following individual active ingredient components and mixture thereof, each individual compound and the mixture being dispersed in 500 liters of water per hectare:

l 3-isopropyl-2,l ,3-benzothiadiazinone-(4)-2 ,2-

dioxide, 1.5 and 2 kg/hectare;

ll 2-sec-butyl-4,o-dinitrophenylacetate, 0.5 and 2 kg/hectare;

l+ ll 1.5 0.5 kg/hectare.

After 8 to 12 days it was ascertained that the mixture had a better herbicidal action than that of its individual components, combined with excellent compatibility with the cereals. The results of this experiment are given below:

2 -isopropyl-3-methyl-4,6-dinitro henol Active ingredient I ll 1 ll Application rate kg/ha L5 2 0.5 2 1.5 0.5

Hordeum vulgare 0 O 20 0 Trilicum aesll'vum O O 0 l 0 Galium aparine 50 80 30 60 I00 Lamium amplexicaule l5 45 5O 90 95 Vitia spp. 30 60 90 Stellar ia media 45 8O 40 80 lOO 0 no damage 100 complete destruction The action of the following mixtures corresponds to that of l II above:

3-isopr'opyl-2, l ,3-benzothiadiazinone-( 4 )-2,2-dioxide,

diethanolamine salt 3-isopropyl-2, l ,3-benzothiadiazinone-( 4 )-2,2-dioxide,

dimethylamine salt 3-isopropyl-2, l ,3-benzothiadiazinone-(4)-2,2-dioxide,

sodium salt 3-isopropyl-2,l,3-benzothiadiazinone-(4)-2,2-dioxide, 20

3-isopropyl-2, l ,3-benzothiadiazinone-(4)-2,2-dioxide, 30

dimethylethanolamine salt 3-isopropyl-2,l ,3-benzothiadiazinone-(4 )-2,2-dioxide,

cyclohexylamine salt 3-sec-butyl-2, l ,3-benzothiadiazinone-( 4)-2,2-dioxide,

dodecylhexamethylenimine salt with . 4 3-isliJpropyl-2, I ,3-benzothiadiazinone-( 4 )-2,2-dioxide wit 2-methyl-4,6-dinitrophenol 2-sec-butyl-4,6-dinitrophenol 2-tert-butyl-4,6-dinitrophenylacetate 2-tert-butyl-5-methyl-4,6-dinitrophenylacetate 2-sec-amyl-4,6-dinitrophenol 2-ethoxymethyl-4,6-dinitrophenol 2-isopropyl-3-methyl-4,6-dinitrophenol 2-( l-methylbutyl)-4,6-dinitrophenol v 2-2,4,5-trichloro-6-nitrophenylchloroacetate.

EXAMPLE 2 In the greenhouse the plants Triticum aestivum, Pisum sativum, Phaseolus spp., Galium aparine, Lamium amplexicaule, Stellaria media and Chenopodium album were treated at a growth height of 2 to 18 cm with the following amounts of the following individual active ingredient components and mixtures thereof, each individual component and each mixture being emulsified or dispersed in 500 liters of water per hectare:

l 3-isopropyl-2,l ,3-benzothiadiazinone-(4)-2,2-

dioxide, 15 and 2 kg/hectare;

ll 3-isopropyl-2,l ,3-benzothiadiazinone-(4)-2,2- dioxide, dimethylamino salt, 1.7 and 2 kg/hectare; Ill 3-sec-butyl-2, l ,3-benzothiadiazinone-( 4 )-2,2-

dioxide, 0.5 and 1.5 kg/hectare; IV 2-methyl-4,6-dinitrophenol, sodium salt, 0.3, 0.5

and 2 kg/hectare; V 2 sec-butyl-4,6-dinitrophenol, l and 1.5 kg/hectare; II W 1.5 0.5 kg/hectare;

ll 1.7 0.3 kg/hectare; lll V 0.5 l kg/hectare.

2-ethoxymethyl-4,6-dinitrophenol 2-methyl-4,o-dinitrophenol 2-sec-butyl-4,6-dinitrophenol 2-tert-butyl-4,6 dinitrophenylacetate 2-tert-butyl-5-methyl-4,6-dinitrophenylacetate 2-sec-butyl-4,6-dinitrophenylacetate 2-sec-amyl-4,o-dinitrophenol 2-( l-methylbutyl)-4,6-dinitrophenol and mixtures of The results show that the mixtures have a herbicidal action superior to that of their individual components.

Active in redient I II III IV kg ha L5 2 1.7 2 0.5 1.5 0.3 0.5

Triticum aeslivum O O O O O 0 O 0 2O Pisum sarivum O O O 5 0 O O 0 l0 Phaseolus spp. O 5 O 5 O O 0 0 l5 Galium aparine 70 5O 65 2O 50 25 35 70 Lamium amplexicaule 10 35 20 25 5 2O 30 90 Ste/[aria media 40 75 20 30 4O Clzenopodium album 40 80 50 7O 20 60 35 40 kg/ha l 1.5 l 5 0.5 l 7 +0.3 0.5 l

Triricum aestivum 0 l0 0 O 0 Pisum sativum 0 5 O 0 0 Phasealus spp. 5 l0 0 O 5 Galium aparine 55 85 100 I00 Lamium amplexicaule 60 85 90 90 90 Ste/[aria media 60 85 I00 100 C'henopodium album 60 90 lOO 100 100 0 no damage I00 complete destruction N 60 We claim:

1. A herbicide composition comprising a herbicidally effective amount of a mixture of a compound of the fo rmula A a R NO R OR where R denotes hydrogen or acetyl, R denotes lower alkyl of a maximum of 6 carbon atoms, R denotes hydrogen or methyl, R denotes nitro, and R denotes hydrogen or methyl, and a compound of the formula /u\ N-R QL M 2. A herbicide composition as claimed in claim 1 wherein compound a is 2-sec-butyl-4,6-dinitrophenylacetate. 

1. A HERBICIDE COMPOSITION COMPRISING A HERBICIDALLY EFFECTIVE AMOUNT OF A MIXTURE OF A COMPOUND OF THE FORMULA
 2. A herbicide composition as claimed in claim 1 wherein compound a is 2-sec-butyl-4,6-dinitrophenylacetate. 